1.0 2011-09-21 01:18:33 UTC 2015-07-21 06:58:58 UTC FDB027010 PI(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) PI(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PI(18:0/22:5(7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the docosapentaenoic acid moiety is derived from fish oils. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol. [HMDB] Atidylinositol(18:0/22:5N3) Atidylinositol(18:0/22:5W3) Phosphatidylinositol(18:0/22:5n3) Phosphatidylinositol(18:0/22:5w3) PI(18:0/22:5n3) PI(18:0/22:5w3) PIno(18:0/22:5n3) PIno(18:0/22:5w3) C49H85O13P 913.1652 912.572779318 [(2R)-2-(docosa-7,10,13,16,19-pentaenoyloxy)-3-(octadecanoyloxy)propoxy]({[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid (2R)-2-(docosa-7,10,13,16,19-pentaenoyloxy)-3-(octadecanoyloxy)propoxy[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphinic acid [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)O[C@@]1([H])C(O)C(O)C(O)[C@@]([H])(O)C1O)OC(=O)CCCCCC=CCC=CCC=CCC=CCC=CCC InChI=1S/C49H85O13P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(51)61-41(40-60-63(57,58)62-49-47(55)45(53)44(52)46(54)48(49)56)39-59-42(50)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,26,28,41,44-49,52-56H,3-4,6,8-10,12,14-16,18,20,23-25,27,29-40H2,1-2H3,(H,57,58)/t41-,44?,45-,46?,47?,48?,49-/m1/s1 QLABQLNIHHHJCI-VEAHQXLZSA-N belongs to the class of organic compounds known as phosphatidylinositols. These are glycerophosphoinositols where the glycerol is esterified with two fatty acids. Phosphatidylinositols Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphoinositols Aliphatic homomonocyclic compounds Carbonyl compounds Carboxylic acid esters Cyclohexanols Dialkyl phosphates Dicarboxylic acids and derivatives Fatty acid esters Hydrocarbon derivatives Inositol phosphates Organic oxides Polyols Alcohol Aliphatic homomonocyclic compound Alkyl phosphate Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cyclic alcohol Cyclitol or derivatives Cyclohexanol Diacylglycerophosphoinositol Dialkyl phosphate Dicarboxylic acid or derivatives Fatty acid ester Fatty acyl Hydrocarbon derivative Inositol phosphate Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organooxygen compound Phosphoric acid ester Polyol Secondary alcohol Solid logp 7.56 ALOGPS logs -6.46 ALOGPS solubility 3.14e-04 g/l ALOGPS logp 10.74 ChemAxon pka_strongest_acidic 1.83 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac [(2R)-2-(docosa-7,10,13,16,19-pentaenoyloxy)-3-(octadecanoyloxy)propoxy]({[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid ChemAxon average_mass 913.1652 ChemAxon mono_mass 912.572779318 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)O[C@@]1([H])C(O)C(O)C(O)[C@@]([H])(O)C1O)OC(=O)CCCCCC=CCC=CCC=CCC=CCC=CCC ChemAxon formula C49H85O13P ChemAxon inchi InChI=1S/C49H85O13P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(51)61-41(40-60-63(57,58)62-49-47(55)45(53)44(52)46(54)48(49)56)39-59-42(50)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,26,28,41,44-49,52-56H,3-4,6,8-10,12,14-16,18,20,23-25,27,29-40H2,1-2H3,(H,57,58)/t41-,44?,45-,46?,47?,48?,49-/m1/s1 ChemAxon inchikey QLABQLNIHHHJCI-VEAHQXLZSA-N ChemAxon polar_surface_area 209.51 ChemAxon refractivity 252.96 ChemAxon polarizability 106.42 ChemAxon rotatable_bond_count 41 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB09820 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 GPI ethanolamine phosphate transferase 1 O95427 PIGN GPI ethanolamine phosphate transferase 2 Q5H8A4 PIGG GPI ethanolamine phosphate transferase 3 Q8TEQ8 PIGO GPI mannosyltransferase 1 Q9H3S5 PIGM GPI mannosyltransferase 2 Q9NUD9 PIGV GPI mannosyltransferase 3 Q92521 PIGB GPI mannosyltransferase 4 Q86VD9 PIGZ GPI transamidase component PIG-S Q96S52 PIGS GPI transamidase component PIG-T Q969N2 PIGT N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase Q9Y2B2 PIGL Phosphatidylinositol 3,4,5-trisphosphate 3-phosphatase TPTE2 Q6XPS3 TPTE2 Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 1 Q92835 INPP5D Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2 O15357 INPPL1 Phosphatidylinositol glycan anchor biosynthesis class U protein Q9H490 PIGU Phosphatidylinositol N-acetylglucosaminyltransferase subunit A P37287 PIGA Phosphatidylinositol N-acetylglucosaminyltransferase subunit C Q92535 PIGC Phosphatidylinositol N-acetylglucosaminyltransferase subunit H Q14442 PIGH Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q Q9BRB3 PIGQ Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y Q3MUY2 PIGY Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha isoform P42336 PIK3CA Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit beta isoform P42338 PIK3CB Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit delta isoform O00329 PIK3CD Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PIK3CG Phosphatidylinositol-glycan biosynthesis class F protein Q07326 PIGF Phosphatidylinositol-glycan biosynthesis class W protein Q7Z7B1 PIGW Phosphatidylinositol-glycan biosynthesis class X protein Q8TBF5 PIGX Phosphatidylserine decarboxylase proenzyme Q9UG56 PISD Phosphatidylserine synthase 1 P48651 PTDSS1 Phosphatidylserine synthase 2 Q9BVG9 PTDSS2 Phospholipase A1 member A Q53H76 PLA1A PI-PLC X domain-containing protein 1 Q9NUJ7 PLCXD1 PI-PLC X domain-containing protein 2 Q0VAA5 PLCXD2 PI-PLC X domain-containing protein 3 Q63HM9 PLCXD3